US20220220076A1 - Quinoline carboxylate compound and preparation method and use thereof - Google Patents

Quinoline carboxylate compound and preparation method and use thereof Download PDF

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Publication number
US20220220076A1
US20220220076A1 US17/600,520 US202017600520A US2022220076A1 US 20220220076 A1 US20220220076 A1 US 20220220076A1 US 202017600520 A US202017600520 A US 202017600520A US 2022220076 A1 US2022220076 A1 US 2022220076A1
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och
compound
sch
formula
hydrogen
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Hui Xu
Jianfeng Tang
Huiwei Chi
Jianting WU
Jun Han
Ying Liu
Baoxiu ZHAO
Zhenguo ZHANG
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SHANDONG UNITED PESTICIDE INDUSTRY Co Ltd
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SHANDONG UNITED PESTICIDE INDUSTRY Co Ltd
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Assigned to SHANDONG UNITED PESTICIDE INDUSTRY CO., LTD. reassignment SHANDONG UNITED PESTICIDE INDUSTRY CO., LTD. ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: CHI, HUIWEI, HAN, JUN, LIU, YING, TANG, JIANFENG, WU, Jianting, XU, HUI, ZHANG, Zhenguo, ZHAO, Baoxiu
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    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
    • A01N43/42—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings condensed with carbocyclic rings
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/84—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms six-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,4
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D215/48—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
    • C07D215/54—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 3
    • C07D215/56—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 3 with oxygen atoms in position 4
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond

Definitions

  • the present disclosure relates to the technical field of agricultural bactericides, and in particular to a quinoline carboxylate compound and a preparation method and use thereof.
  • Bacterial diseases of crop plants are common diseases in agricultural production in China, and are even more harmful than viruses. Bacteria have been a major pathogen second only to fungi. Due to various transmission routes and lack of agents for control as well as long-term successive occurrence, there is increasing difficulty in controlling bacterial diseases. According to incomplete statistics, the current occurrence area of bacterial diseases in China is 120 million mu times, and the market for control of bacterial diseases has a capacity of over 2 billion yuan.
  • agents for controlling bacterial diseases mainly include copper preparations (including organic or inorganic copper preparations) that are heavily used, and antibiotic products, wherein, the copper preparations have low efficacy for bacterial control, and many substances containing heavy metals are sprayed into the environment and thus pollute soil, water and food, causing safety concern over the environment and food; on the other hand, the heavy use of antibiotics may cause resistance of pathogenic bacteria in the human body to medical antibiotics.
  • Only a few types of other agents can be used for treating agricultural bacteria, and can only be applied in a small area, limited by resistance and efficacy in practical production. Therefore, there is an urgent need for the development of a novel, safe and green chemical pesticide with low-toxicity and low-residue.
  • R 1 is selected from hydrogen and halogen
  • R 2 is selected from hydrogen, halogen, C 1 -C 16 alkoxy, halogenated C 1 -C 16 alkoxy, C 3 -C 12 cycloalkoxy, C 1 -C 16 alkylthio, halogenated C 1 -C 16 alkylthio, C 1 -C 16 alkylamino, di(C 1 -C 16 alkyl)amino and 3-12 membered heterocyclyl;
  • R 3 is selected from hydrogen, C 1 -C 16 alkyl and C 3 -C 12 cycloalkyl;
  • n is an integer from 1 to 10, such as 1, 2, 3, 4, 5, 6, 7, 8, 9 and 10.
  • R 1 is selected from hydrogen and halogen
  • R 2 is selected from hydrogen, halogen, C 1 -C 6 alkoxy, halogenated C 1 -C 6 alkoxy, C 3 -C 6 cycloalkoxy, C 1 -C 6 alkylthio, halogenated C 1 -C 6 alkylthio, C 1 -C 6 alkylamino, di(C 1 -C 6 alkyl)amino and 3-10 membered heterocyclyl;
  • R 3 is selected from hydrogen, C 1 -C 6 alkyl and C 3 -C 6 cycloalkyl;
  • n is an integer from 1 to 4.
  • R 1 is selected from hydrogen, fluorine, chlorine, bromine and iodine;
  • R 2 is selected from hydrogen, fluorine, chlorine, bromine, iodine, C 1 -C 4 alkoxy, halogenated C 1 -C 4 alkoxy, C 3 -C 6 cycloalkoxy, C 1 -C 4 alkylthio, halogenated C 1 -C 4 alkylthio, methylamino, ethylamino, dimethylamino, diethylamino,
  • R 3 is selected from hydrogen, C 1 -C 4 alkyl and C 3 -C 6 cycloalkyl;
  • n is an integer from 1 to 4.
  • R 1 is selected from hydrogen, fluorine, chlorine, bromine and iodine
  • R 2 is selected from hydrogen, fluorine, chlorine, bromine, iodine, OCH 3 , OCH 2 CH 3 , OCH 2 CH 2 CH 3 , OCH(CH 3 ) 2 , OCH 2 CH 2 CH 2 CH 3 , OCH 2 CH(CH 3 ) 2 , OCH(CH 3 )(CH 2 CH 3 ), OC(CH 3 ) 3 , OCF 3 , OCHF 2 , OCH 2 CH 2 Cl, OCH 2 CHF 2 , OCH 2 CF 3 , OCH 2 CH 2 CCl 3 ,
  • SCH 3 SCH 2 CH 3 , SCH 2 CH 2 CH 3 , SCH(CH 3 ) 2 , SCH 2 CH 2 CH 2 CH 3 , SCH 2 CH(CH 3 ) 2 , SCH(CH 3 )(CH 2 CH 3 ), SC(CH 3 ) 3 , SCF 3 , SCH 2 CH 2 Cl, SCH 2 CF 3 , NHCH 3 , NHCH 2 CH 3 , N(CH 3 ) 2 , N(CH 2 CH 3 ) 2 ,
  • R 3 is selected from H, CH 3 , CH 2 CH 3 , CH 2 CH 2 CH 3 , CH(CH 3 ) 2 , CH 2 CH 2 CH 2 CH 3 , CH 2 CH(CH 3 ) 2 , CH(CH 3 )(CH 2 CH 3 ), C(CH 3 ) 3 ,
  • n is an integer from 1 to 4.
  • R 1 is selected from hydrogen, fluorine and chlorine
  • R 2 is selected from hydrogen, fluorine, chlorine, OCH 3 , OCH 2 CH 3 , OCH 2 CH 2 CH 3 , OCH(CH 3 ) 2 OCH 2 CH 2 CH 2 CH 3 , OCH 2 CH(CH 3 ) 2 , OCH(CH 3 )(CH 2 CH 3 ), OC(CH 3 ) 3 , OCH 2 CHF 2 , OCH 2 CF 3 , OCH 2 CH 2 CCl 3 ,
  • SCH 3 SCH 2 CH 3 , SCH 2 CH 2 CH 3 , SCH(CH 3 ) 2 , SCH 2 CH 2 CH 2 CH 3 , SCH 2 CH(CH 3 ) 2 , SCH(CH 3 )(CH 2 CH 3 ), SC(CH 3 ) 3 , SCH 2 CH 2 Cl, SCH 2 CF 3 , NHCH 3 , NHCH 2 CH 3 , N(CH 3 ) 2 , N(CH 2 CH 3 ) 2 ,
  • R 3 is selected from H, CH 3 , CH 2 CH 3 , CH 2 CH 2 CH 3 , CH(CH 3 ) 2 , CH 2 CH 2 CH 2 CH 3 , CH 2 CH(CH 3 ) 2 , CH(CH 3 )(CH 2 CH 3 ), C(CH 3 ) 3 ,
  • n is an integer from 1 to 4.
  • R 1 is selected from fluorine and chlorine
  • R 2 is selected from hydrogen, fluorine, chlorine, OCH 3 , OCH 2 CH 3 , OCH 2 CH 2 CH 3 , OCH(CH 3 ) 2 , OCH 2 CH 2 CH 2 CH 3 , OCH 2 CH(CH 3 ) 2 , OCH(CH 3 )(CH 2 CH 3 ), OC(CH 3 ) 3 , OCH 2 CF 3 ,
  • SCH 3 SCH 2 CH 3 , SCH 2 CH 2 CH 3 , SCH(CH 3 ) 2 , SCH 2 CH 2 CH 2 CH 3 , SC(CH 3 ) 3 , NHCH 3 , NHCH 2 CH 3 , N(CH 3 ) 2 , N(CH 2 CH 3 ) 2 ,
  • R 3 is selected from H, CH 3 , CH 2 CH 3 , CH 2 CH 2 CH 3 , CH(CH 3 ) 2 , CH 2 CH 2 CH 2 CH 3 , CH 2 CH(CH 3 ) 2 , CH(CH 3 )(CH 2 CH 3 ) and C(CH 3 ) 3 ;
  • n 2 or 3.
  • the compound of formula (I) is selected from the following compounds,
  • H F CH 2 CH 2 CH 2 CH 3 2 200 H F CH 2 CH(CH 3 ) 2 2 201. H F CH(CH 3 )(CH 2 CH 3 ) 2 202. H F C(CH 3 ) 3 2 203. H F 2 204. H F 2 205. H F 2 206. H F 2 207. H F H 3 208. H F CH 3 3 209. H F CH 2 CH 3 3 210. H F CH 2 CH 2 CH 3 3 211. H F CH(CH 3 ) 2 3 212. H F CH 2 CH 2 CH 2 CH 3 3 213. H F CH 2 CH(CH 3 ) 2 3 214. H F CH(CH 3 )(CH 2 CH 3 ) 3 215. H F C(CH 3 ) 3 3 216.
  • the present disclosure also provides a preparation method of the compound of formula (I) comprising reacting a compound of formula (II) with a compound of formula (III) to give the compound of formula (I),
  • R 1 , R 2 , R 3 and n have the definitions as described above;
  • L is selected from a leaving group, for example, a halogen atom, such as fluorine, chlorine, bromine or iodine.
  • the reaction may be carried out in the presence of a base, wherein the base is selected from an organic base and an inorganic base; and the organic base may be selected from one, two or more of triethylamine, pyridine, etc., and the inorganic base may be selected from one, two or more of sodium carbonate, potassium carbonate, sodium hydroxide, potassium hydroxide, potassium tert-butoxide, sodium hydride, etc.
  • the reaction may be carried out in a solvent, wherein the solvent may be selected from one, two or more of aromatic hydrocarbon solvents, haloalkane solvents, ether solvents, etc., for example, from one, two or more of toluene, dichloromethane, 1,2-dichloroethane, tetrahydrofuran, tert-butyl methyl ether, ethyl acetate, etc.
  • the solvent may be selected from one, two or more of aromatic hydrocarbon solvents, haloalkane solvents, ether solvents, etc., for example, from one, two or more of toluene, dichloromethane, 1,2-dichloroethane, tetrahydrofuran, tert-butyl methyl ether, ethyl acetate, etc.
  • the temperature of the reaction is preferably ⁇ 10° C. to 50° C.
  • the preparation method comprises reacting a compound of formula (V) with a compound of formula (IV) to give the compound of formula (I),
  • R 1 , R 2 , R 3 and n have the definitions as described above;
  • L is selected from a leaving group, for example, a halogen atom, such as fluorine, chlorine, bromine or iodine;
  • M is selected from an alkali metal, such as sodium or potassium.
  • the reaction may be carried out in a solvent, for example, a solvent selected from one, two or more of toluene, 1,2-dichloroethane, acetonitrile, butanone, N,N-dimethylformamide, dimethylsulfoxide, etc.
  • a solvent for example, a solvent selected from one, two or more of toluene, 1,2-dichloroethane, acetonitrile, butanone, N,N-dimethylformamide, dimethylsulfoxide, etc.
  • the temperature of the reaction is preferably 20° C. to 120° C.
  • the compound of formula (II) can be prepared from a compound of formula (II-1),
  • L is selected from a leaving group, for example, a halogen atom, such as fluorine, chlorine, bromine or iodine.
  • the halogenating agent may be selected from an acyl halide of an inorganic acid, for example, phosphorus trichloride, phosphorus pentachloride, thionyl chloride, oxalyl chloride, phosphorus oxychloride and phosphorus tribromide.
  • an acyl halide of an inorganic acid for example, phosphorus trichloride, phosphorus pentachloride, thionyl chloride, oxalyl chloride, phosphorus oxychloride and phosphorus tribromide.
  • the halogenation reaction may be carried out in a solvent, wherein the solvent may be selected from one, two or more of aromatic hydrocarbon solvents, halogenated alkane solvents and alkane solvents, for example, from one, two or more of toluene, 1,2-dichloroethane, petroleum ether, etc.
  • the solvent may be selected from one, two or more of aromatic hydrocarbon solvents, halogenated alkane solvents and alkane solvents, for example, from one, two or more of toluene, 1,2-dichloroethane, petroleum ether, etc.
  • the temperature of the halogenation reaction is preferably 20° C. to 120° C.
  • the compound of formula (V) can be prepared from the compound of formula (II-1),
  • R 1 and R 2 have the definitions as described above; M is selected from an alkali metal, for example, sodium or potassium.
  • the reaction may be carried out in the presence of a base, wherein the base may be selected from one or two of inorganic bases, such as sodium carbonate, potassium carbonate, sodium hydroxide, potassium hydroxide, sodium methoxide, sodium ethoxide, potassium tert-butoxide, sodium hydride, etc.
  • a base may be selected from one or two of inorganic bases, such as sodium carbonate, potassium carbonate, sodium hydroxide, potassium hydroxide, sodium methoxide, sodium ethoxide, potassium tert-butoxide, sodium hydride, etc.
  • the reaction may be carried out in water and/or an organic solvent, for example, in a solvent selected from one or two of water, methanol, ethanol, tetrahydrofuran, etc.
  • the temperature of the reaction is preferably 20° C. to 90° C.
  • the compound of formula (II-1) is commercially available or can be prepared by using a known method.
  • the compound of formula (II-1) can be prepared from a compound of formula (II-2) and a compound of formula (VI),
  • L is selected from a leaving group, for example, a halogen atom, such as fluorine, chlorine, bromine or iodine.
  • the reaction may be carried out in the presence or absence of a base, wherein the base is selected from an organic base or an inorganic base; the organic base may be selected from one, two or more of triethylamine, pyridine, etc., and the inorganic base may be selected from one, two or more of sodium carbonate, potassium carbonate, sodium hydroxide, potassium hydroxide, sodium methoxide, sodium ethoxide, potassium tert-butoxide, sodium hydride, sodium, potassium, etc.
  • the base is selected from an organic base or an inorganic base
  • the organic base may be selected from one, two or more of triethylamine, pyridine, etc.
  • the inorganic base may be selected from one, two or more of sodium carbonate, potassium carbonate, sodium hydroxide, potassium hydroxide, sodium methoxide, sodium ethoxide, potassium tert-butoxide, sodium hydride, sodium, potassium, etc.
  • the reaction may be carried out in a solvent, wherein the solvent may be selected from one, two or more of aromatic hydrocarbon solvents, amide solvents, sulfone solvents, etc., for example, from one, two or more of toluene, N-methylpyrrolidone, N,N-dimethylformamide, N,N-dimethylacetamide, dimethylsulfoxide, etc.
  • the solvent may be selected from one, two or more of aromatic hydrocarbon solvents, amide solvents, sulfone solvents, etc., for example, from one, two or more of toluene, N-methylpyrrolidone, N,N-dimethylformamide, N,N-dimethylacetamide, dimethylsulfoxide, etc.
  • the temperature of the reaction is preferably 50° C. to 150° C.
  • the compound of formula (II-1) can also be prepared by reacting the compound of formula (II-2) with a metal salt (VI-1) of the compound of formula (VI),
  • R 1 and R 2 have the definitions as described above;
  • L is selected from a leaving group, for example, a halogen atom, such as fluorine, chlorine, bromine or iodine;
  • M is selected from an alkali metal, for example, sodium or potassium.
  • the reaction may be carried out in a solvent, wherein the solvent may be selected from one, two or more of aromatic hydrocarbon solvents, amide solvents, sulfone solvents, etc., for example, from one, two or more of toluene, N-methylpyrrolidone, N,N-dimethylformamide, N,N-dimethylacetamide, dimethylsulfoxide, etc.
  • the solvent may be selected from one, two or more of aromatic hydrocarbon solvents, amide solvents, sulfone solvents, etc., for example, from one, two or more of toluene, N-methylpyrrolidone, N,N-dimethylformamide, N,N-dimethylacetamide, dimethylsulfoxide, etc.
  • the temperature of the reaction is preferably 50° C. to 150° C.
  • the compound of formula (II-1) can also be commercially available or can be prepared by using a known method:
  • R 1 and R 2 have the definitions as described above; R′ is selected from alkyl, such as methyl or ethyl.
  • the R 2 may be selected from hydrogen and halogen, such as hydrogen, fluorine, chlorine, bromine or iodine.
  • the compound of formula (II-2) can be commercially available or can be prepared by a known method, for example:
  • the reaction can be carried out with reference to a piror literature or a similar method thereof.
  • the compounds of formulas (X) and (X-1) can also be commercially available or can be prepared by a known method.
  • suitable reaction conditions and starting materials can be selected according to different situations.
  • one substituent can be substituted with another substituent according to the present disclosure in a one-step reaction, or more substituents can be substituted with other substituents according to the present disclosure in the same reaction step.
  • the compounds can not be obtained via the above synthetic routes, they can be prepared by deriving other compounds of formula (I) or by conventionally changing the synthetic routes.
  • the reaction mixture can be post-treated by a conventional method, such as purifying a crude product by mixing with water, phase separation and chromatography, for example, on alumina or silica gel.
  • An isomer mixture of the compound of formula (I) can be obtained by using the above preparation method. If a pure isomer is desired, the separation can be performed by a conventional method such as crystallization or chromatography.
  • the present disclosure also provides a use of at least one compound of formula (I) for preparing a bactericide for use in the agricultural field.
  • the present disclosure also provides a use of at least one compound of formula (I) as a bactericide for use in the agricultural field.
  • the present disclosure also provides a composition comprising at least one compound of formula (I) as an active ingredient.
  • the present disclosure also provides a use of the composition as a bactericide for use in the agricultural field.
  • the composition is a bactericidal composition.
  • the bactericide is preferably a crop bactericide or a plant bactericide.
  • the present disclosure also provides a method for controlling bacteria (for example, phytopathogens) or diseases caused thereby, comprising applying an effective amount of at least one compound of formula (I) or the composition to a growth medium for the bacteria or diseases.
  • bacteria for example, phytopathogens
  • diseases caused thereby comprising applying an effective amount of at least one compound of formula (I) or the composition to a growth medium for the bacteria or diseases.
  • the compound of formula (I) can be used for controlling the following bacteria or diseases caused thereby:
  • Gram-negative bacteria erwinia (causing fire blight in pears, etc.); genus pectobacterium (causing soft rot in cruciferous vegetables, black shank in potatoes, etc.); dikia (causing stem rot in sweet potatoes, bacterial stem rot in maize, bacterial basal rot in rice, black shank in potatoes, rust in pears, etc.); pantoea (causing bacterial wilt in maize, leaf spot by pantoea in maize, bacterial leaf blight in rice beans, canker in drupes, etc.); pseudomonas (causing canker in peaches, bacterial blight in peas, bacterial black spot in crucifer, bacterial leaf spot disease in tomatoes, bacterial spot disease in tomatoes, bacterial black spot in rape, bacterial angular leaf spot in sesame, bacterial angular leaf spot in cucumbers, tobacco wildfire, bacterial brown spot in maize, bacterial stem blight in broad beans, bacterial spot in soybeans, bacterial
  • Gram-positive bacteria clavibacterium (causing ring rot in potatoes, bacterial canker in tomatoes, bacterial wilt in alfalfa, Goss's bacterial wilt and blight in maize, bacterial mosaic in wheat, etc.); streptomyces (mildew) (causing scab disease in potatoes, etc.); curtobacterium (causing bacterial wilt in kidney beans, yellow blister spot in tulips, wilt disease in kidney beans, etc.); arthrobacter (causing leaf blight in winterberries, etc.); rhodococcus (causing fasciation disease in sweet peas, etc.); bacillus (causing bacterial leaf spot by bacillus in maize, white leaf streak in wheat, etc.); rhizoctonia (causing spike blight in cat grass etc.).
  • the above-mentioned compounds can advantageously be used for protecting important agricultural and horticultural crops or plants from damage by bacterial germs.
  • the amount of the compound used to achieve the desired effect will vary depending upon various factors, for example, the compound used, the crop to be protected, the type of the pest, the infection level, the climatic conditions, the route of application and the dosage form employed.
  • ingredients of the dosage forms or compositions described herein are selected in accordance with the physical properties of the active ingredient, the route of application and environmental factors such as the soil type, moisture and temperature.
  • Such dosage forms include liquid agents such as solutions (including emulsifiable concentrates), suspensions and emulsions (including microemulsions and/or suspensions), which may optionally be viscous gels.
  • the dosage forms also include solids such as powders, granules, tablets, pills, films, which may be water-dispersible (“wettable”) or water-soluble.
  • the effective ingredient can be microencapsulated and made into suspension or solid dosage form; in addition, the entire dosage form of the active ingredient may also be encapsulated.
  • the capsule can control or delay the release of the effective ingredient.
  • Sprayable dosage forms can be diluted in a suitable medium, and the spray volume used is about one to several hundred liters per hectare.
  • the composition with high concentration is mainly used as an intermediate for further processing.
  • Typical solid diluents are described in Watkins et al, Handbook of Insecticide Dust Diluents and Carriers, 2nd Ed., Dorland Books, Caldwell, N.J. Typical liquid diluents are described in Marsden, SolventsGuide, 2nd Ed., Interscience, New York, 1950. Surfactants and recommended applications are listed in McCutcheon's Detergents and Emulsifiers Annual , Allued Publ. Corp., Ridgewood, N.J., and Sisely and Wood, Encyclopedia of Surface Active Agents , Chemical Publishing Co., Inc., New York, 1964. All dosage forms may contain small amounts of additives to reduce foaming, prevent caking, prevent corrosion, prevent microbial growth, etc., or be added with thickeners to increase viscosity.
  • Surfactants include, for example, polyethoxylated alcohols, polyethoxylated alkylphenols, polyethoxylated sorbitan fatty acid esters, sulfonated dialkyl succinates, alkyl sulfates, alkyl benzene sulfonates, organosilanes, N,N-dialkyl taurates, lignosulfonates, aldehyde condensates for naphthalene sulfonates, polycarboxylates, and polyoxyethylene/polyoxypropylene block copolymers.
  • Solid diluents include, for example, clays such as bentonite, montmorillonite, attapulgite and kaolin, starches, sugars, silica, talc, celite, urea, calcium carbonate, sodium bicarbonate, sodium sulfate; liquid diluents include, for example, water, N,N-dimethylformamide, dimethylsulfone, N-alkylpyrrolinone, ethylene glycol, polypropylene glycol, paraffin, alkylbenzene, alkylnaphthalene, olive oil, castor oil, linseed oil, tung oil, sesame oil, corn oil, peanut oil, cottonseed oil, soybean oil, rapeseed oil and cacao oil, fatty acid esters, ketones such as cyclohexanone, 2-heptanone, isophorone and 4-hydroxy-4-methyl-2-pentanone, and alcohols such as methanol, cyclohexanol, dode
  • Solutions can be prepared by simply mixing the components.
  • Powders and fines may be prepared by mixing or by grinding, usually in a hammer mill or fluid-energy mill.
  • Suspensions are typically prepared by wet milling, for example by the method described in U.S. Pat. No. 3,060,084.
  • Granules and pills are prepared by spraying the active substance onto freshly prepared granular carriers or by granulation techniques. See Browning, “Agglomeration”, Chemical Engineering , Dec. 4, 1967, 147-48 ; Perry's Chemical Engineer's Handbook, 4th Ed., McGraw-Hill, New York, 1963, 8-57; and WO 9113546. Pills are prepared by the method described in U.S. Pat. No.
  • compositions described herein for certain applications of the composition, for example, in agriculture, one, two or more of other bactericides, insecticides, acaricides, herbicides, plant growth regulators or fertilizers, etc. can be added to the composition described herein, thereby bringing additional advantages and effects.
  • groups and substituents thereof can be selected by those skilled in the art to provide stable moieties and compounds.
  • substituents When a substituent is described by a general formula written from left to right, the substituent also includes chemically equivalent substituents that are obtained when the formula is written from right to left.
  • CH 2 O is equivalent to OCH 2 .
  • a numerical range defined by only “integer” is recited in the specification and claims of this application, it shall be construed as reciting both endpoints of the range and every integer within the range. For example, an “integer from 1 to 10” should be understood to include every integer of 1, 2, 3, 4, 5, 6, 7, 8, 9 and 10.
  • halogen refers to fluorine, chlorine, bromine or iodine.
  • C 1 -C 16 alkyl refers to a linear or branched saturated monovalent hydrocarbyl group having 1-16 carbon atoms, preferably C 1 -C 10 alkyl.
  • C 1 -C 10 alkyl preferably refers to a linear or branched saturated monovalent hydrocarbyl group having 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10 carbon atoms.
  • the alkyl is, for example, methyl, ethyl, propyl, butyl, pentyl, hexyl, isopropyl, isobutyl, sec-butyl, tert-butyl, isopentyl, 2-methylbutyl, 1-methylbutyl, 1-ethylpropyl, 1,2-dimethylpropyl, neopentyl, 1,1-dimethylpropyl, 4-methylpentyl, 3-methylpentyl, 2-methylpentyl, 1-methylpentyl, 2-ethylbutyl, 1-ethylbutyl, 3,3-dimethylbutyl, 2,2-dimethylbutyl, 1,1-dimethylbutyl, 2,3-dimethylbutyl, 1,3-dimethylbutyl or 1,2-dimethylbutyl, or isomers thereof.
  • the group has 1, 2, 3, 4, 5 or 6 carbon atoms (“C 1 -C 6 alkyl”), and is, for example, methyl, ethyl, propyl, butyl, isopropyl, isobutyl, sec-butyl, tert-butyl, pentyl or hexyl; more particularly, the group is a linear or branched saturated monovalent hydrocarbyl group having 1, 2, 3 or 4 carbon atoms.
  • the alkyl is, for example, methyl, ethyl, propyl, butyl, isopropyl, isobutyl, sec-butyl, tert-butyl or isomers thereof.
  • alkyl such as “C 1 -C 6 alkyl”
  • C 1 -C 6 alkyl are also applicable to other terms containing “C 1 -C 6 alkyl”, for example, the terms “C 1 -C 6 alkoxy”, “halogenated C 1 -C 6 alkoxy”, “C 1 -C 6 alkylthio”, “halogenated C 1 -C 6 alkylthio”, and “C 1 -C 6 alkylamino”.
  • C 3 -C 12 cycloalkyl refers to a saturated monovalent monocyclic or bicyclic hydrocarbon ring having 3-12 carbon atoms, preferably “C 3 -C 10 cycloalkyl”.
  • C 3 -C 10 cycloalkyl refers to a saturated monovalent monocyclic or bicyclic hydrocarbon ring having 3, 4, 5, 6, 7, 8, 9 or 10 carbon atoms.
  • the C 3 -C 10 cycloalkyl may be a monocyclic hydrocarbyl group such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl or cyclodecyl, or a bicyclic hydrocarbyl group such as a decahydronaphthalene ring.
  • the group has 3, 4, 5 or 6 carbon atoms, and is, for example, cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl.
  • cycloalkyl such as “C 3 -C 6 cycloalkyl”, are also applicable to other terms containing “C 3 -C 6 cycloalkyl”, for example, the terms “C 3 -C 6 cycloalkoxy”, “C 3 -C 6 cycloalkylamino” and “oxo C 3 -C 6 cycloalkylamino”.
  • 3-12 membered heterocyclyl refers to a saturated monovalent monocyclic or bicyclic hydrocarbon ring comprising 1-5 heteroatoms independently selected from N, O and S, and preferably is “3-10 membered heterocyclyl”.
  • the term “3-10 membered heterocyclyl” refers to a saturated monovalent monocyclic or bicyclic ring comprising 1-5, preferably 1-3, heteroatoms selected from N, O and S.
  • the heterocyclyl may be connected to the rest of the molecule through any of the carbon atoms or the nitrogen atom (if present).
  • the heterocyclyl may include, but is not limited to: 4 membered rings such as azetidinyl or oxetanyl; 5 membered rings such as tetrahydrofuranyl, dioxolyl, pyrrolidinyl, imidazolidinyl, pyrazolidinyl or pyrrolinyl; 6 membered rings such as tetrahydropyranyl, piperidinyl, morpholinyl, dithianyl, thiomorpholinyl, piperazinyl or trithianyl; or 7 membered rings such as diazepanyl. More particularly, the heterocyclyl is a 6 membered ring containing at least 1 nitrogen atom, through which the heterocyclyl is connected to the rest of the molecule.
  • haloalkyl refers to a linear or branched alkyl group where the hydrogen atoms are partially or fully replaced by halogen atoms, for example, CF 3 CH 2 —.
  • alkoxy refers to a linear or branched alkyl group that is bonded to the structure through an oxygen atom, for example, CH 3 CH 2 O—.
  • haloalkoxy refers to an alkoxy group where the hydrogen atoms of the alkyl group may be partially or fully replaced by halogen atoms, for example, ClCH 2 CH 2 O—.
  • alkylthio refers to a linear or branched alkyl group that is bonded to the structure through a sulfur atom, for example, CH 3 CH 2 S—.
  • haloalkylthio refers to an alkylthio group where the hydrogen atoms of the alkyl group may be partially or fully replaced by halogen atoms, for example, ClCH 2 CH 2 S—.
  • alkylamino refers to a linear or branched alkyl group that is bonded to the structure through a nitrogen atom, for example, CH 3 CH 2 NH—.
  • di(alkyl)amino refers to 2 linear or branched alkyl groups that are bonded to the structure through a nitrogen atom, for example, (CH 3 CH 2 ) 2 N—.
  • the compounds of formula (I) disclosed herein show excellent activity against various bacterial germs in the agricultural field. Moreover, the compounds can achieve an excellent control effect at a very low dosage, and thus can be used for preparing bactericides, particularly bactericides for crops or plants.
  • the compounds are further proved to have good activity for improving the growth and development of crops, to be capable of promoting the height growth of plants, to stimulate the synthesis of chlorophyll and increase the leaf area of the plants, so that the leaves of the crops are greener and thicker, and the photosynthetic efficiency is thus improved, which indirectly improves the immunity of the plants and the capability of resisting the adverse external environment, and makes the plants more robust.
  • the compounds of the present disclosure are easy to prepare and high in yield, and thus have good prospects for application.
  • 1,2-dihydroxyethane (0.62 g, 0.01 mol) and triethylamine (2.02 g, 0.02 mol) were sequentially dissolved in dichloromethane (20 mL) at room temperature.
  • the reaction mixture was cooled to 0° C. in a cooling bath.
  • the above mixture was added dropwise with a solution of 7-chloro-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carbonyl chloride (2.85 g, 0.0095 mol) in dichloromethane (10 mL). After the dropwise addition, the mixture was allowed to naturally warm to room temperature, and reacted for 4 h.
  • the reaction mixture was added with a saturated aqueous sodium bicarbonate solution (10 mL) and extracted with dichloromethane (15 mL ⁇ 3). The organic phases were combined, washed with water (15 mL ⁇ 1), washed with saturated brine (10 mL ⁇ 1), and dried over anhydrous magnesium sulfate. The crude product was precipitated under reduced pressure, and recrystallized from toluene to give the product (2.32 g, 75% yield).
  • the reaction mixture was added with a saturated aqueous sodium bicarbonate solution (10 mL) and extracted with dichloromethane (15 mL ⁇ 3). The organic phases were combined, washed with water (15 mL ⁇ 1), washed with saturated brine (10 mL ⁇ 1), and dried over anhydrous magnesium sulfate. The crude product was precipitated under reduced pressure, and recrystallized from toluene to give the product (2.83 g, 88% yield).
  • 1,2-dihydroxypropane (0.76 g, 0.01 mol) and triethylamine (2.02 g, 0.02 mol) were dissolved sequentially in dichloromethane (20 mL) at room temperature.
  • the reaction mixture was cooled to 0° C. in a cooling bath.
  • the above mixture was added dropwise with a solution of 7-chloro-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carbonyl chloride (2.85 g, 0.0095 mol) in dichloromethane (10 mL). After the dropwise addition, the mixture was allowed to naturally warm to room temperature, and reacted for 4 h.
  • the reaction mixture was added with a saturated aqueous sodium bicarbonate solution (10 mL) and extracted with dichloromethane (15 mL ⁇ 3). The organic phases were combined, washed with water (15 mL ⁇ 1), washed with saturated brine (10 mL ⁇ 1), and dried over anhydrous magnesium sulfate. The crude product was precipitated under reduced pressure, and recrystallized from toluene to give the product (2.22 g, 69% yield).
  • the reaction mixture was added with a saturated aqueous sodium bicarbonate solution (10 mL) and extracted with dichloromethane (15 mL ⁇ 3). The organic phases were combined, washed with water (15 mL ⁇ 1), washed with saturated brine (10 mL ⁇ 1), and dried over anhydrous magnesium sulfate. The crude product was precipitated under reduced pressure, and recrystallized from toluene to give the product (2.83 g, 84% yield).
  • the reaction mixture was added with a saturated aqueous sodium bicarbonate solution (8 mL) and extracted with dichloromethane (10 mL ⁇ 3). The organic phases were combined, washed with water (10 mL ⁇ 1), washed with saturated brine (10 mL ⁇ 1), and dried over anhydrous magnesium sulfate. The crude product was precipitated under reduced pressure, and recrystallized from toluene to give the product (1.82 g, 82% yield).
  • the reaction mixture was added with a saturated aqueous sodium bicarbonate solution (8 mL) and extracted with dichloromethane (10 mL ⁇ 3). The organic phases were combined, washed with water (10 mL ⁇ 1), washed with saturated brine (10 mL ⁇ 1), and dried over anhydrous magnesium sulfate. The crude product was precipitated under reduced pressure, and recrystallized from toluene to give the product (1.46 g, 88% yield).
  • the reaction mixture was added with a saturated aqueous sodium bicarbonate solution (8 mL) and extracted with dichloromethane (10 mL ⁇ 3). The organic phases were combined, washed with water (10 mL ⁇ 1), washed with saturated brine (10 mL ⁇ 1), and dried over anhydrous magnesium sulfate. The crude product was precipitated under reduced pressure, and recrystallized from toluene to give the product (1.52 g, 85% yield).
  • the reaction mixture was added with a saturated aqueous sodium bicarbonate solution (10 mL) and extracted with dichloromethane (10 mL ⁇ 3). The organic phases were combined, washed with water (10 mL ⁇ 1), washed with saturated brine (10 mL ⁇ 1), and dried over anhydrous magnesium sulfate. The crude product was precipitated under reduced pressure, and recrystallized from toluene to give the product (1.95 g, 86% yield).
  • the reaction mixture was added with a saturated aqueous sodium bicarbonate solution (8 mL) and extracted with dichloromethane (10 mL ⁇ 3). The organic phases were combined, washed with water (10 mL ⁇ 1), washed with saturated brine (10 mL ⁇ 1), and dried over anhydrous magnesium sulfate. The crude product was precipitated under reduced pressure, and recrystallized from toluene to give the product (1.9 g, 81% yield).
  • the compound obtained in the above example was used to prepare a wettable powder, which was specifically prepared from the starting materials of the following ratios: Compound 151, 60.0%; dodecylphenol polyethoxy glycol ether, 4.0%; sodium lignosulfonate, 5.0%; sodium aluminosilicate, 6.0%; and montmorillonite (calcined), 25.0%.
  • the compound obtained in the above example was used to prepare a granule, which was specifically prepared from the starting materials of the following ratios:
  • Compound 152 10.0%; and the other components are sodium dodecyl sulfate, 2%; calcium lignosulfonate, 6%; potassium chloride, 10%; polydimethylsiloxane, 1%; and soluble starch making up the rest.
  • Compound 164 25.0%; anhydrous calcium sulfate, 10.0%; crude calcium lignosulfonate, 5.0%; sodium alkyl naphthalene sulfonate, 1.0%; and calcium/magnesium bentonite, 59.0%.
  • Compound 165 25.0%; solvent 150, 60%; PEG 400, 5%; Rhodacal 70/B, 3%; and Rhodameen RAM/7, 7%.
  • the compound of the present disclosure shows good activity against various bacterial germs in the agricultural field.
  • the compounds of the present disclosure were tested for in vitro bacteriostatic activity or in vivo protective effect against various bacterial diseases in plants, and for effect of improving the growth and development of crops.
  • the results of the assay for bactericidal activity and the effect of improving the growth and development of crops are shown in the following examples.
  • the test method is as follows: the agent was formulated and diluted to a range of concentrations with a suitable solvent (such as acetone, methanol, N,N-dimethylformamide and dimethylsulfoxide, and was selected according to its capability of dissolving the sample).
  • a suitable solvent such as acetone, methanol, N,N-dimethylformamide and dimethylsulfoxide, and was selected according to its capability of dissolving the sample.
  • a suitable solvent such as acetone, methanol, N,N-dimethylformamide and dimethylsulfoxide
  • test results of the in vitro bacteriostatic activity (shown as inhibitory rates) of part of the compounds against the pathogenic bacteria causing bacterial angular leaf spot in cucumbers are as follows:
  • the compounds having an inhibitory rate of no less than 90% for the pathogenic bacteria causing bacterial angular leaf spot in cucumbers comprise: 1, 2, 10, 18, 44, 45, 143, 144, 151, 152, 153, 160, 164, 165, 177, 178, 194, 195, 207, 208, 264, 265, 270, 275, 281, 282, 287, 292, 294, 296, 300, 307, 309, 312, 315, 320, 323, 326, 329, 335, 342, 353, 360, 364, 371, 372, 381, 382, 390, 397, 400, 401, 407, 408, 413, 414, 419, 420, 425, 426, 431 and 432.
  • the control agents oxine-copper and zhongshengmycin have inhibitory rates of 2% and 48% for the pathogenic bacteria causing bacterial angular leaf spot in cucumbers, respectively.
  • the compounds having an inhibitory rate of no less than 90% for the pathogenic bacteria causing bacterial angular leaf spot in cucumbers comprise: 10, 45, 151, 152, 153, 164, 165, 177, 178, 195, 207, 208, 264, 265, 270, 275, 281, 282, 287, 292, 294, 296, 300, 307, 309, 312, 315, 320, 323, 326, 329, 335, 342, 371, 372, 381, 382, 390, 397, 400, 401, 407, 408, 413, 414, 419, 420, 425, 426, 431 and 432; the compounds having an inhibitory rate of no less than 80% comprise: 1, 18, 44, 143, 144, 160, 194, 353, 360 and 364.
  • the control agents oxine-copper and zhongshengmycin have inhibitory rates of 0% and 21% for the pathogenic bacteria causing bacterial angular leaf
  • the compounds having an inhibitory rate of no less than 90% for the pathogenic bacteria causing bacterial wilt in tobacco comprise: 1, 2, 10, 18, 44, 45, 143, 144, 151, 152, 153, 160, 164, 165, 177, 178, 194, 195, 207, 208, 264, 265, 270, 275, 281, 282, 287, 292, 294, 296, 300, 307, 309, 312, 315, 320, 323, 326, 329, 335, 342, 353, 360, 364, 371, 372, 381, 382, 390, 397, 400, 401, 407, 408, 413, 414, 419, 420, 425, 426, 431 and 432.
  • the control agents oxine-copper and zhongshengmycin have inhibitory rates of 5% and 51% for the pathogenic bacteria causing bacterial wilt in tobacco, respectively.
  • the compounds having an inhibitory rate of no less than 90% for the pathogenic bacteria causing bacterial wilt in tobacco comprise: 45, 151, 152, 153, 164, 165, 177, 178, 195, 207, 208, 264, 265, 270, 275, 281, 282, 287, 292, 294, 296, 300, 307, 309, 312, 315, 320, 323, 326, 329, 335, 342, 371, 372, 381, 382, 390, 397, 400, 401, 407, 408, 413, 414, 419, 420, 425, 426, 431 and 432; the compounds having an inhibitory rate of no less than 80% comprise: 1, 10, 18, 44, 143, 144, 160, 194, 353, 360 and 364.
  • the control agents oxine-copper and zhongshengmycin have inhibitory rates of 0% and 28% for the pathogenic bacteria causing bacterial wilt in tobacco
  • the compounds having an inhibitory rate of no less than 90% for the pathogenic bacteria causing black shank in potatoes comprise: 1, 2, 10, 18, 44, 45, 143, 144, 151, 152, 153, 160, 164, 165, 177, 178, 194, 195, 207, 208, 264, 265, 270, 275, 281, 282, 287, 292, 294, 296, 300, 307, 309, 312, 315, 320, 323, 326, 329, 335, 342, 353, 360, 364, 371, 372, 381, 382, 390, 397, 400, 401, 407, 408, 413, 414, 419, 420, 425, 426, 431 and 432.
  • the control agents oxine-copper and zhongshengmycin have inhibitory rates of 3% and 55% for the pathogenic bacteria causing black shank in potatoes, respectively.
  • the compounds having an inhibitory rate of no less than 90% for the pathogenic bacteria causing black shank in potatoes comprise: 45, 151, 152, 153, 164, 165, 177, 195, 207, 208, 264, 265, 270, 275, 281, 282, 287, 292, 294, 296, 300, 307, 309, 312, 315, 320, 323, 326, 329, 335, 342, 371, 372, 381, 382, 390, 397, 400, 401, 407, 408, 413, 414, 419, 420, 425, 426, 431 and 432; the compounds having an inhibitory rate of no less than 80% comprise: 1, 10, 18, 44, 143, 144, 160, 178, 194, 353, 360 and 364.
  • the control agents oxine-copper and zhongshengmycin have inhibitory rates of 0% and 38% for the pathogenic bacteria causing black shank in potatoes, respectively.
  • the compounds having an inhibitory rate of no less than 90% for the pathogenic bacteria causing stem rot in sweet potatoes comprise: 1, 2, 10, 18, 44, 45, 143, 144, 151, 152, 153, 160, 164, 165, 177, 178, 194, 195, 207, 208, 264, 265, 270, 275, 281, 282, 287, 292, 294, 296, 300, 307, 309, 312, 315, 320, 323, 326, 329, 335, 342, 353, 360, 364, 371, 372, 381, 382, 390, 397, 400, 401, 407, 408, 413, 414, 419, 420, 425, 426, 431 and 432.
  • the control agents oxine-copper and zhongshengmycin have inhibitory rates of 7% and 46% for the pathogenic bacteria causing stem rot in sweet potatoes, respectively.
  • the compounds having an inhibitory rate of no less than 90% for the pathogenic bacteria causing stem rot in sweet potatoes comprise: 10, 45, 151, 152, 153, 164, 165, 177, 178, 195, 207, 208, 264, 265, 270, 275, 281, 282, 287, 292, 294, 296, 300, 307, 309, 312, 315, 320, 323, 326, 329, 335, 342, 371, 372, 381, 382, 390, 397, 400, 401, 407, 408, 413, 414, 419, 420, 425, 426, 431 and 432; the compounds having an inhibitory rate of no less than 80% comprise: 1, 18, 44, 143, 144, 160, 194, 353, 360 and 364.
  • the control agents oxine-copper and zhongshengmycin have inhibitory rates of 2% and 25% for the pathogenic bacteria causing stem rot in sweet potatoes, respectively.
  • test results of the in vitro bacteriostatic activity (shown as inhibitory rates) of part of the compounds against the pathogenic bacteria causing bacterial blight in rice are as follows:
  • the compounds having an inhibitory rate of no less than 90% for the pathogenic bacteria causing bacterial blight in rice comprise: 1, 2, 10, 18, 44, 45, 143, 144, 151, 152, 153, 160, 164, 165, 177, 178, 194, 195, 207, 208, 264, 265, 270, 275, 281, 282, 287, 292, 294, 296, 300, 307, 309, 312, 315, 320, 323, 326, 329, 335, 342, 353, 360, 364, 371, 372, 381, 382, 390, 397, 400, 401, 407, 408, 413, 414, 419, 420, 425, 426, 431 and 432.
  • the control agents oxine-copper and zhongshengmycin have inhibitory rates of 16% and 48% for the pathogenic bacteria causing bacterial blight in rice, respectively.
  • the compounds having an inhibitory rate of no less than 90% for the pathogenic bacteria causing bacterial blight in rice comprise: 45, 151, 152, 153, 164, 165, 178, 195, 207, 208, 264, 265, 270, 275, 281, 282, 287, 292, 294, 296, 300, 307, 309, 315, 320, 323, 326, 329, 335, 342, 371, 372, 381, 382, 390, 397, 400, 401, 407, 408, 413, 414, 419, 420, 425, 426, 431 and 432; the compounds having an inhibitory rate of no less than 80% comprise: 1, 10, 18, 44, 143, 144, 160, 177, 194, 312, 353, 360 and 364.
  • the control agents oxine-copper and zhongshengmycin have inhibitory rates of 9% and 30% for the pathogenic bacteria causing bacterial blight in rice, respectively.
  • the compounds having an inhibitory rate of no less than 90% for the pathogenic bacteria causing fruit blotch in watermelons comprise: 1, 2, 10, 18, 44, 45, 143, 144, 151, 152, 153, 160, 164, 165, 177, 178, 194, 195, 207, 208, 264, 265, 270, 275, 281, 282, 287, 292, 294, 296, 300, 307, 309, 312, 315, 320, 323, 326, 329, 335, 342, 353, 360, 364, 371, 372, 381, 382, 390, 397, 400, 401, 407, 408, 413, 414, 419, 420, 425, 426, 431 and 432.
  • the control agents oxine-copper and zhongshengmycin have inhibitory rates of 3% and 52% for the pathogenic bacteria causing fruit blotch in watermelons, respectively.
  • the compounds having an inhibitory rate of no less than 90% for the pathogenic bacteria causing fruit blotch in watermelons comprise: 10, 45, 151, 152, 153, 164, 165, 177, 178, 195, 207, 208, 264, 265, 270, 275, 281, 282, 287, 292, 294, 296, 300, 307, 309, 312, 315, 320, 323, 326, 329, 335, 342, 371, 372, 381, 382, 390, 397, 400, 401, 407, 408, 413, 414, 419, 420, 425, 426, 431 and 432; the compounds having an inhibitory rate of no less than 80% comprise: 1, 18, 44, 143, 144, 160, 194, 353, 360 and 364.
  • the control agents oxine-copper and zhongshengmycin have inhibitory rates of 0% and 29% for the pathogenic bacteria causing fruit blotch in water
  • the compounds having an inhibitory rate of no less than 90% for the pathogenic bacteria causing black rot in Chinese cabbages comprise: 1, 2, 10, 18, 44, 45, 143, 144, 151, 152, 153, 160, 164, 165, 177, 178, 194, 195, 207, 208, 264, 265, 270, 275, 281, 282, 287, 292, 294, 296, 300, 307, 309, 312, 315, 320, 323, 326, 329, 335, 342, 353, 360, 364, 371, 372, 381, 382, 390, 397, 400, 401, 407, 408, 413, 414, 419, 420, 425, 426, 431 and 432.
  • the control agents oxine-copper and zhongshengmycin have inhibitory rates of 5% and 46% for the pathogenic bacteria causing black rot in Chinese cabbages, respectively.
  • the compounds having an inhibitory rate of no less than 90% for the pathogenic bacteria causing black rot in Chinese cabbages comprise: 10, 45, 151, 152, 153, 164, 165, 177, 178, 195, 207, 208, 264, 265, 270, 275, 281, 282, 287, 292, 294, 296, 300, 307, 309, 312, 315, 320, 323, 326, 329, 335, 342, 371, 372, 381, 382, 390, 400, 401, 407, 408, 413, 414, 419, 420, 425, 426, 431 and 432; the compounds having an inhibitory rate of no less than 80% comprise: 1, 18, 44, 143, 144, 160, 194, 353, 360, 364 and 397.
  • the control agents oxine-copper and zhongshengmycin have inhibitory rates of 0% and 19% for the pathogenic bacteria causing black rot in Chinese cabbages,
  • test results of the in vitro bacteriostatic activity (shown as inhibitory rates) of part of the compounds against the pathogenic bacteria causing bacterial wilt in cassava are as follows:
  • the compounds having an inhibitory rate of no less than 90% for the pathogenic bacteria causing bacterial wilt in cassava comprise: 1, 2, 10, 18, 44, 45, 143, 144, 151, 152, 153, 160, 164, 165, 177, 178, 194, 195, 207, 208, 264, 265, 270, 275, 281, 282, 287, 292, 294, 296, 300, 307, 309, 312, 315, 320, 323, 326, 329, 335, 342, 353, 360, 364, 371, 372, 381, 382, 390, 397, 400, 401, 407, 408, 413, 414, 419, 420, 425, 426, 431 and 432.
  • the control agents oxine-copper and zhongshengmycin have inhibitory rates of 15% and 51% for the pathogenic bacteria causing bacterial wilt in cassava, respectively.
  • the compounds having an inhibitory rate of no less than 90% for the pathogenic bacteria causing bacterial wilt in cassava comprise: 10, 45, 151, 152, 153, 164, 165, 177, 178, 195, 207, 208, 264, 265, 270, 275, 281, 282, 287, 292, 294, 296, 300, 307, 309, 312, 315, 320, 323, 326, 329, 335, 342, 371, 372, 381, 382, 390, 397, 400, 401, 407, 408, 413, 414, 419, 420, 425, 426, 431 and 432; the compounds having an inhibitory rate of no less than 80% comprise: 1, 18, 44, 143, 144, 160, 194, 353, 360 and 364.
  • the control agents oxine-copper and zhongshengmycin have inhibitory rates of 7% and 32% for the pathogenic bacteria causing bacterial wilt
  • the compounds having an inhibitory rate of no less than 90% for the pathogenic bacteria causing fire blight in pears comprise: 1, 2, 10, 18, 44, 45, 143, 144, 151, 152, 153, 160, 164, 165, 177, 178, 194, 195, 207, 208, 264, 265, 270, 275, 281, 282, 287, 292, 294, 296, 300, 307, 309, 312, 315, 320, 323, 326, 329, 335, 342, 353, 360, 364, 371, 372, 381, 382, 390, 397, 400, 401, 407, 408, 413, 414, 419, 420, 425, 426, 431 and 432.
  • the control agents oxine-copper and zhongshengmycin have inhibitory rates of 3% and 43% for the pathogenic bacteria causing fire blight in pears, respectively.
  • the compounds having an inhibitory rate of no less than 90% for the pathogenic bacteria causing fire blight in pears comprise: 10, 45, 151, 152, 153, 164, 165, 177, 178, 195, 207, 208, 264, 265, 270, 275, 281, 282, 287, 292, 294, 296, 300, 307, 309, 312, 315, 320, 323, 326, 329, 335, 342, 371, 372, 381, 382, 390, 400, 401, 407, 408, 413, 414, 419, 420, 425, 426, 431 and 432; the compounds having an inhibitory rate of no less than 80% comprise: 1, 18, 44, 143, 144, 160, 194, 353, 360, 364 and 397.
  • the control agents oxine-copper and zhongshengmycin have inhibitory rates of 0% and 23% for the pathogenic bacteria causing fire blight in pears,
  • the compound to be tested was dissolved in a small amount of a suitable solvent (such as acetone, methanol, N,N-dimethylformamide and dimethyl sulfoxide, and was selected according to its capability of dissolving the sample), and then diluted to the concentration for tests with 0.1% tween 80.
  • a suitable solvent such as acetone, methanol, N,N-dimethylformamide and dimethyl sulfoxide, and was selected according to its capability of dissolving the sample
  • the pathogenic bacteria cultured to stationary phase were well mixed with a fixed amount of the compound solution, and the sprouted melon seeds, tomato seeds, tobacco seeds and potato seeds were soaked in the mixture of the bacterial suspension and the compound for half an hour. Then the seeds were sowed in a culture cup containing earthworm castings, and placed in a greenhouse for moisture preservation and culture. The efficacy investigation was performed after the control seeds were adequately diseased.
  • the surfaces of the Chinese cabbage leaves were pricked to form wounds using an inoculation needle, and 5 ⁇ L of the soft rot bacteria cultured to stationary phase were added into the wounds for inoculation.
  • the materials for tests were placed in an incubator for a 48 h incubation in the dark, and the efficacy investigation was performed after the control seeds were adequately diseased.
  • the compound to be tested was dissolved in a small amount of a suitable solvent (such as acetone, methanol, N,N-dimethylformamide and dimethyl sulfoxide, and was selected according to its capability of dissolving the sample), and then diluted to the desired concentration with water.
  • a suitable solvent such as acetone, methanol, N,N-dimethylformamide and dimethyl sulfoxide, and was selected according to its capability of dissolving the sample
  • the aqueous solution of the compound was sprayed on the surface of a plant material for tests. After the solution on the surface was dried in a shady place, the suspension of the pathogenic bacteria cultured to stationary phase was sprayed on the surface of the plant material for tests for inoculation, and then the plant material for tests was placed into a greenhouse for moisture preservation and culture.
  • the culture was carried out for about ten days, and the efficacy investigation was performed after the control seeds were adequately diseased.
  • the compound to be tested was dissolved in a small amount of a suitable solvent (such as acetone, methanol, N,N-dimethylformamide and dimethyl sulfoxide, and was selected according to its capability of dissolving the sample), and then diluted to the desired concentration with water. Root irrigation was carried out on the potatoes for tests according to the designed concentration of the agents. The dosage for each plant was 200 mL and was kept consistent (also for the control). The black shank bacteria were inoculated on the second day after the application. The results were investigated according to the disease condition.
  • a suitable solvent such as acetone, methanol, N,N-dimethylformamide and dimethyl sulfoxide
  • the compounds having efficacy of no less than 90% against bacterial angular leaf spot in cucumbers comprise: 1, 2, 10, 18, 44, 45, 143, 144, 151, 152, 153, 160, 164, 165, 177, 178, 194, 195, 207, 208, 264, 265, 270, 275, 281, 282, 287, 292, 294, 296, 300, 307, 309, 312, 315, 320, 323, 326, 329, 335, 342, 353, 360, 364, 371, 372, 381, 382, 390, 397, 400, 401, 407, 408, 413, 414, 419, 420, 425, 426, 431 and 432.
  • the control agents oxine-copper and zhongshengmycin have efficacy of 15% and 20% against bacterial angular leaf spot in cucumbers, respectively.
  • the compounds having efficacy of no less than 90% against bacterial angular leaf spot in cucumbers comprise: 10, 45, 151, 152, 153, 164, 165, 177, 178, 195, 207, 208, 264, 265, 270, 275, 281, 282, 287, 292, 294, 296, 300, 307, 309, 312, 315, 320, 323, 326, 329, 335, 342, 371, 372, 381, 382, 390, 397, 400, 401, 407, 408, 413, 414, 419, 420, 425, 426, 431 and 432; the compounds having efficacy of no less than 80% comprise: 1, 18, 44, 143, 144, 160, 194, 353, 360 and 364.
  • the control agents oxine-copper and zhongshengmycin have efficacy of 10% and 12% against bacterial angular leaf spot in cucumbers, respectively.
  • the compounds having efficacy of no less than 90% against bacterial wilt in tobacco comprise: 1, 2, 10, 18, 44, 45, 143, 144, 151, 152, 153, 160, 164, 165, 177, 178, 194, 195, 207, 208, 264, 265, 270, 275, 281, 282, 287, 292, 294, 296, 300, 307, 309, 312, 315, 320, 323, 326, 329, 335, 342, 353, 360, 364, 371, 372, 381, 382, 390, 397, 400, 401, 407, 408, 413, 414, 419, 420, 425, 426, 431 and 432.
  • the control agents oxine-copper and zhongshengmycin have efficacy of 11% and 35% against bacterial wilt in tobacco, respectively.
  • the compounds having efficacy of no less than 90% against bacterial wilt in tobacco comprise: 1, 2, 10, 18, 44, 45, 143, 144, 151, 152, 153, 160, 164, 165, 177, 178, 194, 195, 207, 208, 264, 265, 270, 275, 281, 282, 287, 292, 294, 296, 300, 307, 309, 312, 315, 320, 323, 326, 329, 335, 342, 353, 360, 364, 371, 372, 381, 382, 390, 397, 400, 401, 407, 408, 413, 414, 419, 420, 425, 426, 431 and 432.
  • the control agents oxine-copper and zhongshengmycin have efficacy of 5% and 24% against bacterial wilt in tobacco, respectively.
  • the compounds having efficacy of no less than 90% against black shank in potatoes comprise: 1, 2, 10, 18, 44, 45, 143, 144, 151, 152, 153, 160, 164, 165, 177, 178, 194, 195, 207, 208, 264, 265, 270, 275, 281, 282, 287, 292, 294, 296, 300, 307, 309, 312, 315, 320, 323, 326, 329, 335, 342, 353, 360, 364, 371, 372, 381, 382, 390, 397, 400, 401, 407, 408, 413, 414, 419, 420, 425, 426, 431 and 432.
  • the control agents oxine-copper and zhongshengmycin have efficacy of 22% and 25% against black shank in potatoes, respectively.
  • the compounds having efficacy of no less than 90% against black shank in potatoes comprise: 151, 152, 153, 164, 165, 177, 195, 207, 208, 264, 265, 275, 281, 282, 287, 292, 294, 296, 300, 307, 309, 312, 315, 320, 323, 326, 329, 335, 342, 371, 372, 381, 382, 390, 397, 400, 401, 407, 408, 413, 414, 419, 420, 425, 426, 431 and 432; the compounds having efficacy of no less than 80% comprise: 1, 10, 18, 44, 45, 143, 144, 160, 178, 194, 270, 353, 360 and 364.
  • the control agents oxine-copper and zhongshengmycin have efficacy of 11% and 17% against black shank in potatoes, respectively.
  • the compounds having efficacy of no less than 90% against stem rot in sweet potatoes comprise: 1, 2, 10, 18, 44, 45, 143, 144, 151, 152, 153, 160, 164, 165, 177, 178, 194, 195, 207, 208, 264, 265, 270, 275, 281, 282, 287, 292, 294, 296, 300, 307, 309, 312, 315, 320, 323, 326, 329, 335, 342, 353, 360, 364, 371, 372, 381, 382, 390, 397, 400, 401, 407, 408, 413, 414, 419, 420, 425, 426, 431 and 432.
  • the control agents oxine-copper and zhongshengmycin have efficacy of 20% and 38% against stem rot in sweet potatoes, respectively.
  • the compounds having efficacy of no less than 90% against stem rot in sweet potatoes comprise: 1, 2, 10, 18, 44, 45, 143, 144, 151, 152, 153, 160, 164, 165, 177, 178, 194, 195, 207, 208, 264, 265, 270, 275, 281, 282, 287, 292, 294, 296, 300, 307, 309, 312, 315, 320, 323, 326, 329, 335, 342, 353, 360, 364, 371, 372, 381, 382, 390, 397, 400, 401, 407, 408, 413, 414, 419, 420, 425, 426, 431 and 432.
  • the control agents oxine-copper and zhongshengmycin have efficacy of 13% and 23% against stem rot in sweet potatoes, respectively.
  • the compounds having efficacy of no less than 90% against bacterial blight in rice comprise: 1, 2, 10, 18, 44, 45, 143, 144, 151, 152, 153, 160, 164, 165, 177, 178, 194, 195, 207, 208, 264, 265, 270, 275, 281, 282, 287, 292, 294, 296, 300, 307, 309, 312, 315, 320, 323, 326, 329, 335, 342, 353, 360, 364, 371, 372, 381, 382, 390, 397, 400, 401, 407, 408, 413, 414, 419, 420, 425, 426, 431 and 432.
  • the control agents oxine-copper and zhongshengmycin have efficacy of 10% and 35% against bacterial blight in rice, respectively.
  • the compounds having efficacy of no less than 90% against bacterial blight in rice comprise: 151, 152, 153, 164, 165, 178, 195, 207, 208, 264, 265, 270, 275, 281, 282, 287, 292, 294, 296, 300, 307, 309, 315, 320, 323, 326, 329, 335, 342, 371, 372, 381, 382, 390, 397, 400, 401, 407, 408, 413, 414, 419, 420, 425, 426, 431 and 432; the compounds having efficacy of no less than 80% comprise: 1, 10, 18, 44, 45, 143, 144, 160, 177, 194, 312, 353, 360 and 364.
  • the control agents oxine-copper and zhongshengmycin have efficacy of 6% and 24% against bacterial blight in rice, respectively.
  • the compounds having efficacy of no less than 90% against fruit blotch in watermelons comprise: 1, 2, 10, 18, 44, 45, 143, 144, 151, 152, 153, 160, 164, 165, 177, 178, 194, 195, 207, 208, 264, 265, 270, 275, 281, 282, 287, 292, 294, 296, 300, 307, 309, 312, 315, 320, 323, 326, 329, 335, 342, 353, 360, 364, 371, 372, 381, 382, 390, 397, 400, 401, 407, 408, 413, 414, 419, 420, 425, 426, 431 and 432.
  • the control agents oxine-copper and zhongshengmycin have efficacy of 22% and 33% against fruit blotch in watermelons, respectively.
  • the compounds having efficacy of no less than 90% against fruit blotch in watermelons comprise: 1, 2, 10, 18, 44, 45, 143, 144, 151, 152, 153, 160, 164, 165, 177, 178, 194, 195, 207, 208, 264, 265, 270, 275, 281, 282, 287, 292, 294, 296, 300, 307, 309, 312, 315, 320, 323, 326, 329, 335, 342, 353, 360, 364, 371, 372, 381, 382, 390, 397, 400, 401, 407, 408, 413, 414, 419, 420, 425, 426, 431 and 432.
  • the control agents oxine-copper and zhongshengmycin have efficacy of 15% and 19% against fruit blotch in watermelons, respectively.
  • the compounds having efficacy of no less than 90% against soft rot in Chinese cabbages comprise: 1, 2, 10, 18, 44, 45, 143, 144, 151, 152, 153, 160, 164, 165, 177, 178, 194, 195, 207, 208, 264, 265, 270, 275, 281, 282, 287, 292, 294, 296, 300, 307, 309, 312, 315, 320, 323, 326, 329, 335, 342, 353, 360, 364, 371, 372, 381, 382, 390, 397, 400, 401, 407, 408, 413, 414, 419, 420, 425, 426, 431 and 432.
  • the control agents oxine-copper and zhongshengmycin have efficacy of 16% and 39% against soft rot in Chinese cabbages, respectively.
  • the compounds having efficacy of no less than 90% against soft rot in Chinese cabbages comprise: 151, 152, 153, 164, 165, 177, 178, 195, 207, 208, 264, 265, 270, 275, 281, 282, 287, 292, 294, 296, 300, 307, 309, 312, 315, 320, 323, 326, 329, 335, 342, 371, 372, 381, 382, 390, 400, 401, 407, 408, 413, 414, 419, 420, 425, 426, 431 and 432; the compounds having efficacy of no less than 80% comprise: 1, 10, 45, 18, 44, 143, 144, 160, 194, 353, 360, 364 and 397.
  • the control agents oxine-copper and zhongshengmycin have effic
  • RI-rate of growth rate increase in percent (%)
  • the longitudinal and transverse diameters i.e., leaf length and leaf width, respectively, wherein the leaf length is the distance from the base to the tip of a leaf, and leaf width is the measured value of the upper shoulder width of the leaf
  • leaf length is the distance from the base to the tip of a leaf
  • leaf width is the measured value of the upper shoulder width of the leaf
  • SI-rate of leaf area increase in percent (%)
  • the chlorophyll contents of leaves were measured by using a chlorophyll measuring instrument (model: SPAD-520 Plus).
  • SPI-chlorophyll content increase in percent (n);
  • the compounds of the present disclosure have no adverse effect on the crops for tests, and are safe enough to meet the safety requirements of green pesticides.
  • the compounds of the present disclosure have particular positive physiological effects on crops as follows: promoting the height growth of plants, stimulating the synthesis of chlorophyll and increasing the leaf area of the plants, so that the leaves of the crops are greener and thicker and thus improving the photosynthetic efficiency, which directly improves the immunity of the plants and the capability of resisting the adverse external environment, and makes the plants more robust.
  • the doses of the compounds 152 and 282 of the present disclosure (both prepared as dispersible granules with a mass fraction of 10%) used were 16.87 ga.i./hm 2 and 33.75 ga.i./hm 2 , and the control agents used were 3% (by weight) wettable powder of zhongshengmycin and 33.5% (by weight) aqueous suspension of oxine-copper (both were commercially available).
  • the dose of zhongshengmycin was 67.5 ga.i./hm 2
  • the dose of oxine-copper was 337.5 ga.i./hm 2 .
  • Test and control agents were arranged in randomized blocks. Plot area was 15 m 2 . Treatment was repeated 3 times. The route of application was spraying on stem and leaves. The application was performed 2 times in total at an interval of 7 days, and the efficacy investigation was performed 7 days after the last application. During the investigation, sampling was carried out at 5 points in each plot. Disease conditions of soft rot in Chinese cabbages, soft rot in lettuces and soft rot in wild cabbages were recorded according to the relevant technical standard of Pesticide Guidelines for the Field Efficacy Trials GB/T17980.114-2004, and the incidence rate of plants was calculated to further evaluate the control effect.

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CN109912504B (zh) * 2019-04-04 2020-11-10 山东省联合农药工业有限公司 一种喹啉羧酸类化合物及其制备方法与用途
CN110551124B (zh) * 2019-06-14 2021-01-08 山东省联合农药工业有限公司 一种喹诺酮类化合物或其农药学上可接受的盐及其制备方法与用途
WO2022089447A1 (zh) * 2020-10-26 2022-05-05 山东省联合农药工业有限公司 一种含喹诺酮类化合物的增效杀菌组合物及其应用
CN114467949B (zh) * 2020-10-26 2023-08-25 山东省联合农药工业有限公司 一种含喹诺酮类化合物的增效组合物及其应用
CN114467967B (zh) * 2020-10-26 2023-08-25 山东省联合农药工业有限公司 一种含喹诺酮类化合物和铜制剂的增效杀菌组合物
CN116941624A (zh) * 2021-04-29 2023-10-27 山东省联合农药工业有限公司 一种杀菌杀虫组合物及其应用
WO2024104344A1 (zh) * 2022-11-16 2024-05-23 沈阳中化农药化工研发有限公司 一种喹啉羧酸衍生物及其用途

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